Michael Wynn paused, arms extended, waiting for the next order telling him to lower his body to the floor. He had survived his plebe year at the US Naval Academy, but graduation was still a long way off. Like most of his class, Wynn had arrived at Navy convinced that aviation was the only path for him. The movie Top Gun had come out two years before, and every Navy recruit was lining up to become the next Maverick.

As he dropped again and strained to raise his body off the floor, the upperclassmen hovering over him suggested a new path. Wynn was a short ex-wrestler with bad eyes. He stood little chance of winning the ultra competitive race for aviation. Instead, the upperclassmen told him, his background as a boy scout made him perfect for the Marines.

Aware of the fact that life commanding 12 grunts required more communication training, Wynn switched his major from the sciences to English. Shortly after that, he went home to Pittsfield, took some courses at Berkshire Community College, and transferred to Williams to focus more fully on the liberal arts.

After an injury ended his military career and poor eyesight kept him out of the federal law enforcement agencies, Wynn settled on a career as a police officer in his hometown. Fourteen years after his college graduation, Wynn became one of the youngest police chiefs in Pittsfield history.

I met up with Wynn in his Pittsfield office to learn about his journey into law enforcement and day-to-day life as a cop.